How To Style Leggings And Still Look Chic

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Love ‘ em or hate ’em, leggings have made a comeback and are definitely here to stay. Like plenty of pieces ( hello, leopard! ) from years past, a pair of leggings is here for a while.

To be honest, a pair of great leggings are one of those wardrobe staples that no one should be without. Generally speaking, plain black leggings are the pair that you will certainly reach for. 

Casual Leggings Outfit

When done right, your favorite leggings can look hip and sophisticated. Of course, the opposite is also true – when done wrong, it appears sloppy and messy.

The right leggings provide the perfect middle ground between casual wear and a going out look.

An oversized blazer and heels provide the pieces for a classy look, that can even be worn in an office. A boxy tee and sleek sneakers are perfect for a coffee run. 

Scroll below to find inspo for casual leggings outfits to wear throughout the cooler months.

1. Trench Coat

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Instagram @oliviafaeh

Black leggings have become so ubiquitous in our day-to-day rotation that they probably get more wear-time than almost any other item in your wardrobe.

Start off with stretch athletic leggings and a sports bra, which epitomize ease and elegance.

Styling-wise, layer on a timeless trench coat for trips from the gym to a casual brunch with friends.

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Instagram @orlaithmelia_


It’s no secret that classic black leggings are a go-to when it comes to athleisure—and these wear-with-everything airbrush leggings are at the top of our shopping list.

Lean into the athletic nature of the sporty style leggings, however, try a pair in a fun color to switch out the typical black pair.

2. Jackets

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Instagram @valeriya_orl

For the ultimate styling hack, style basic black leggings for the winter months with a faux fur coat and high boots.

A faux-fur coat will even dress up the most basic of pieces for the ultimate winter look. 

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Instagram @gettyimages

Luxe faux leather leggings are the ultimate day-to-night delight. Leather leggings are a classic item because they’re versatile and instantly add an edgy vibe to any outfit.

Take a style cue from Gigi, and up the ante and style the staple alongside a leather bomber and slouchy boots.

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Instagram @melissa_thiebaut

Like any closet classic, there are plenty of outfit ideas to style the staple. However, the best options are the most comfortable.

A pair of leggings are the definition of chic, especially when styled with a totally trending shearling jacket and city chic sneakers.

Other minimalist must-haves in the mix include a baseball cap, and a luxury handbag.

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Instagram @moyamii


Leather is a great option to pair with form-fitting leggings and a pair of pointed-toe heels.

The addition of the pop of color from the dress shirt keeps the look fresh, while the black leather tote is a quietly luxurious addition.

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Instagram @vladislava.r

Remember that old faux pas about brown and black being the ultimate style taboo? Consider it stricken from the record: the non-traditional color combo is currently having a major moment.

Swap out the usual jean jacket for a luxe suede piece to add an elevated element to the casual style of leggings. 

3. Blazers

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Instagram @morganmaurice

When temperatures dip, add a solid color blazer into the equation.  From a black blazer to chocolate brown, all colors and silhouettes are welcome.

Add a modern twist by adding split-hem leggings. Positioned to the front, these split-hem leggings were made to be worn with pointed-toe shoes or ankle boots.  

Add a pair of pointed-toe boots, and you’ll look like you have legs for days.

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Instagram @its.me.romy


A blazer is not just for stuffy office environments, it can be the perfect casual setting piece.

Styling-wise, follow suit and wear an oversized blazer and a pair of it-girl sneakers.  

The result? A look that is as smart as it is stylish. Baggy, oversized jackets and knitwear are an easy way to keep cozy in leggings. 

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Instagram @jordannasharp

Enter: the office-appropriate way to wear leggings. 

Yes, the the leggings-and-blazer combo are perfect for a fashion-forward work environment. Add a thin leather belt to cinch and define the waist. 

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Instagram @aliceoliviac

You can’t deny the power of a modern blazer in a looser shape or with a sweater over your shoulder to add that touch of cool to a look.

The beauty of a textured jacket is that it will bring an instantly elevated vibe to any look, including an ensemble with leggings.

Effortlessly chic.

4. Sweatshirt

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Instagram @brooklynblonde1


More comfortable than jeans and with the ability to look incredibly sleek, leggings shouldn’t be overlooked when assembling your trans-seasonal outfits.

They form a solid base to set interesting separates against and are pretty low-maintenance in terms of upkeep and cleaning.

Add an oversized sweatshirt or hoodie to the equation for a put together easy look. 

5. Sweaters

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Instagram @gokceseymabulut

Stirrup leggings are also a favorite among the street style scene, with fashion forward women sporting pairs with everything from notable knitwear to blazers.

Pair a more traditional striped sweater and chunky loafers with stirrup leggings for an outfit that feels timeless and trendy all at once. 

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Instagram @nlmarilyn

Styling-wise, keep the minimalist moment going with a tailored camel coat and a pair of camel boots.

It is the kind of outfit that will take you from fall to spring. 

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Instagram @marianna_hewitt

A classic striped cardigan sweater easily becomes a statement piece when it is paired with leggings and bold patent leather boots.  

The shiny leather boots suddenly makes a casual outfit, not so casual anymore.